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In the previous article on the joys and pitfalls of freeing your Apple portable devices from Steve Jobs technoid BDSM prison, we briefly discussed the advantages and disadvantages of jailbreak. In this article we get a bit more hands-on and look at the actual methods of achieving this. Although just released, iPad has already been jailbroken (see video below) and an announcement will be made about iPhone OS 4.0 soon.

Most jailbreaking tools are tied to a specific firmware release. You can either read your firmware version and then download whichever tool works for you – what most people do or upgrade / downgrade to a version for which you can easily find a jailbreaking tool. I have an iPhone and and iPod and don’t have time or the desire to play with too many applications, especially pirated. I have enough free applications and games to choose from and of the apps on my iPhone, I hardly use only 4 or 5 frequently. As such, I kept my devices as bought for a long time. I recently decided to jailbreak my iPod as I was under the mistaken belief that you cannot use Skype or any VOIP on 3G and was thinking of using the iPod as training for jailbreaking the iPhone. After learning that I can actually use a SIP client, I have no reason to proceed with the jailbreak.

Based on my research, I recommend the following steps:

1. f0recast

Download and run f0recast with your phone connected to your computer and iTunes closed. For my iPhone and iPod I got the following results:

This means that both my iPhone and my iPod can be jailbroken. They are also both not tethered, which means that if the battery drains or if I turn the device off, I will not need a computer to boot it up again. Though I’m not sure, I suspect “unlocking” in this context refers to the ability to unlock the phone from my cell phone provider, which would allow me to insert another provider’s SIM card and use it natively (non-roaming) on their network. The application suggests using blacksn0w, the other option, valid only in different circumstances, being ultrasn0w.

2. update (or downgrade) firmware

If necessary, update your device to the latest firmware you can find a jailbreaking tool for. You normally accomplish this by clicking Restore in iTunes device page while holding the Shift key. If that does not work, consider using iREB, which you can download using the link in sources, below. (This step is unconnected to the previous, so you could’ve started here.)

Jailbreaking has a bad habit of not working unless the firmware has been freshly restored. Keep in mind though that restoring is more difficult for the later firmware versions. Some firmware upgrades, such as 3.1.3, are currently a one-way street: once you upgrade, the baseband gets upgraded as well and you cannot downgrade easily. See the previous article for more information on this topic.

3. weapon of choice

To commence jailbreaking, you might want to connect your device by USB, then close iTunes. In Windows XP, it is a good idea to stop iTunes Helper, the service that causes iTunes to start (you can do so by launching services.msc from the Run.. dialogue box, invoked by pressing WindowsKey + R).

My first attempt was with a very old version of redsn0w (possibly the first), which I found in one of my folders – I first wanted to perform this action long time ago but did not, due to lack of time. That was, as expected, unsuccessful:

Either connect your iPod in DFU mode to the computer or just push enter for assisted entry into DFU mode

Hit any key to continue...

DEVICE PREPARATION ------------------

0. Make sure your iPod both turned off and connected to the computer. Hold down the Hold (top left corner) button until the 'Slide to power off' message appears, and then slide the button to turn off the device

Hit any key to continue...

1. Follow the next steps carefully. Things will appear and disappear on the iPod screen, not necessarily timed with your actions. Ignore them and focus on the directions

I also tried the latest stable version of redsn0w but without a fresh firmware:

Needless to say, that was unsuccessful. I even tried sn0wbreeze on my iPod and that failed as well:

Finally, I refreshed once again the firmware only that this time I did not restore the full backup, setting up my iPod as a new. For most situations, the blackra1n gives the fastest and possibly the easiest jailbreak. It is a very simple application, containing a single button:

As for differences between the tools, it is worth mentioning that redsn0w is the only tool that works on Linux, in addition of Windows and Mac. PwnageTool works solely on Mac, while sn0wbreeze is Windows only. Blackra1n aims to be universal, while purplera1n works only on iPhone 3GS. Unlike Blackra1n, redsn0w can also optionally modify your boot logo, make the boot verbose and perform (in version 0.9.3) the IPCC tethering hack, which allows for other, unsigned Carrier Bundles to be installed. This permits tethering (i.e., using your phone as an Internet modem for your laptop).

4. post-install

Blackra1n will install only a black tear – when you click it, you have an option of runnig either Cydia or Rock. Though everybody is using Cydia, you might find it unbearably slow. Rock is supposed to be faster, but I haven’t tried it. Redsn0w installs Cydia by default.

Don’t install both Cydia and Rock or you might run into problems.

Of the many things you can do, you might want to do immediately after the jailbreaking is complete and you installed on “free app store” is to install the MobileTerminal package, which provides terminal emulation. Start the Terminal, the gain root with “su root”. The default password is “alpine”. To change it, issue the command “passwd”. This is an important password that will prevent worms from taking over your device, so make sure you can remember it easily and it’s difficult for others to guess it. You should also change the regular user account password with “passwd mobile”.

Install then the OpenSSH package. Connect from your desktop with “ssh root@<ip-address-of-your-device>”. Your program will generate some crypto keys so that you don’t have to enter a password all the time. If the connection is slow, consider turning off QoS on your Router – though if you are using VOIP behind the router you might not want to do just that.

Other applications you might want to install are:

Backgrounder – allows for applications to run in the background; e.g., let FlyCast play while you read the news or do your email.